Sodium Hydroxide → HCID 702850, compound

HRID 919368Notes

Reaction equation

HRID 919368 reaction equation
[C:1](=[N:9][OH:10])([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].C([N+](C)(C)C)C1C=CC=CC=1.[OH-].[Na+].[O:25]1[CH:29]=[CH:28][CH:27]=[C:26]1[C:30](Cl)=O>CC1CCCO1.O>[C:2]1([C:1]2[N:8]=[C:30]([C:26]3[O:25][CH:29]=[CH:28][CH:27]=3)[O:10][N:9]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 682422-Furancarbonyl chlorideHCID 69186N'-Hydroxybenzenecarboximidamide

Product 1

HCID 702850HCID 702850, compoundYield 64.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 73012-MethyltetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Benzamide oxime (2.00 g, 14.7 mmol) and a 40% aqueous solution of benzyltrimethylammonium hydroxide (100 uL) were combined in 2-methyltetrahydrofuran (20 mL) and water (2 mL). The solution was warmed to 50° C. and 50% aqueous solution of sodium hydroxide (1.52 g, 19.1 mmol) and 2-furoyl chloride (2.00 g, 15.3 mmol) were added dropwise simultaneously over 10 min. The pot temperature rose to 74° C. The mixture was stirred at 60° C. for 48 hours and the solids dissolved. The mixture was cooled to room temperature and poured into water (25 mL). The 2-methyltetrahydrofuran was removed at reduced pressure and solids formed in the aqueous solution. The solids were collected by vacuum filtration. 3-phenyl-5-(2-furanyl)-1,2,4-oxadiazole (2.33 g, 9.5 mmol) was obtained as a white solid. (64% yield).

Workup

  1. customrose to 74° C
  2. dissolutionthe solids dissolved
  3. temperatureThe mixture was cooled to room temperature
  4. customThe 2-methyltetrahydrofuran was removed at reduced pressure and solids
  5. customformed in the aqueous solution
  6. filtrationThe solids were collected by vacuum filtration

Sources & evidence

ORD record
ord-4ff3ca7725dd460d8335a12e01e3604e
Source dataset
uspto-grants-2016_03
Patent number
US09273037B2

Reaction notes

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